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Volumn 31, Issue 27, 1990, Pages 3905-3908

The first synthesis of chiral phosphinocarboxylic acid ligands, trans-2-(diphenylphosphino)cycloalkanecarboxylic acids. The phosphine-palladium complexes catalyzed asymmetric allylic alkylation

(5) Okada, Yoshiharu a Minami, Toru a Sasaki, Yoritaka a Umezu, Yasuo a Yamaguchi, Masahiko a

a KYUSHU INSTITUTE OF TECHNOLOGY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE;

ARTICLE; NONHUMAN; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0025283910 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)97502-6 Document Type: Article

Times cited : (33)

References (21)

1
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- A preliminary account of these results has been reported at 16th Symposium on Organic Sulfur and Phosphorus Chemistry of the Chemical Society of Japan, Morioka, January, 1989; abstract p. 131.

2
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- Knowles¹ Sabacky²

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- Asymmetric Catalytic Hydrogenation with an Optically Active Phosphinerhodium Complex in Homogeneous Solution
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- Horner¹ Siegel² Buthe³

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- Kagan¹ Dang²

5
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- o-Diphenylphosphinobenzoic acid, an achiral phosphinocarboxylic acid ligand, has been used as an active catalyst for ethylene oligomerization in its nickel complex: R.F. Mason, United States Patent, 3686351 (1972)

6
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- For reviews
- (1977) Tetrahedron , vol.33 , pp. 2615
- Trost¹

7
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- (1986) Tetrahedron , vol.42 , pp. 4361
- Tsuji¹

8
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- For recent Palladium catalyzed asymmetric allylic alkylation:
- (1989) Chem. Rev. , vol.89 , pp. 257
- Consiglio¹ Waynouth²

9
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- (1977) J. Am. Chem. Soc. , vol.99 , pp. 1649
- Trost¹ Strege²

10
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- (1985) J. Am. Chem. Soc. , vol.107 , pp. 2033
- Auburn¹ Mackenzie² Bosnich³

11
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- (1986) Tetrahedron Lett. , vol.27 , pp. 191
- Hayashi¹ Yamamoto² Hagihara³ Ito⁴

12
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- (1983) J. Org. Chem. , vol.48 , pp. 2569
- Minami¹ Sako² Ikehira³ Hanamoto⁴ Hirao⁵

13
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- 1-Alkenyl- und 1-Cycloalkenylphosphonium-Salze durch Selenenylierung von Phosphor-Yliden und anschließende Seleninsäure-Eliminierung
- (1979) Chemische Berichte , vol.112 , pp. 355
- Saleh¹ Minami² Ohshiro³ Agawa⁴

14
- 84914376662
- 2P: C, 71.82; H, 6.03. Found: C, 71.55; H, 5.99.

15
- 84914376661
- The enantiomeric purities of 6a,b, 11, 12, and 13 were determined by HPLC analysis of the corresponding diastereomeric amides prepared from the carboxylic acids 6a, b, 14, 15, and 16 and (−)-PEA in the presence of 2-chloro-1-methylpyridinium iodide and triethylamine.

16
- 84914376660
- 2).

17
- 0001276112
- Synthesis and resolution of a new type of chiral bisphosphine ligand, trans-bis-1,2-(diphenylphosphino)cyclobutane, and asymmetric hydrogenation using its rhodium complex.
- (1986) Chemistry Letters , pp. 613
- Minami¹ Okada² Nomura³ Hirota⁴ Nagahara⁵ Fukuyama⁶

18
- 33845183545
- A related effect of a hydroxy group in chiral ferrocenylphosphine ligands on asymmetric induction has been recently discussed on the palladium-catalyzed asymmetric allylic amination, see:
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 6301
- Hayashi¹ Yamamoto² Ito³ Nishioka⁴ Miura⁵ Yanagi⁶

19
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- The first observation of syn-anti dichotomy in the formation of (.pi.-allyl)palladium complexes
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- Stary¹ Kocovsky²

20
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- Marino¹ Farina²

21
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- The enantiomeric purity of 17 was determined by HPLC analysis of its diastereomeric 6-[(−)-(α methylbenzylamido)-vinyl]cyclohex-2-en-1-ol (48%, 43% ee) which was obtained by the reaction of 17 with lithium (−)-α-methylbenzylamide, generated in situ from (−)-PEA with n-BuLi in dry THF.

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